Iodine → HCID 178506076, compound

HRID 246657Notes

Reaction equation

HRID 246657 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[CH:5][CH:4]=1.[OH-].[K+].[I:16]I.C(OCC)(=O)C>CN(C=O)C>[I:16][C:7]1[C:6]2[C:10](=[CH:11][C:3]([C:2]([F:1])([F:12])[F:13])=[CH:4][CH:5]=2)[NH:9][N:8]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 214555996-(trifluoromethyl)-1H-indazole

Product 1

HCID 178506076HCID 178506076, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(trifluoromethyl)-1H-indazole (0.5 g, 2.69 mmol), KOH (0.45 g, 8.1 mmol) and I2 (1.37 g, 5.38 mmol) in dry DMF (20 mL) was stirred for 16 hours at room temperature. Ethyl acetate (100 mL) was added and the mixture was washed with water (3×10 mL) and brine (2×10 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was then washed with ether (2 mL) and filtered to afford 3-iodo-6-(trifluoromethyl)-1H-indazole (688 mg, crude) as a yellow solid. LCMS: (M+H)+=313.

Workup

  1. washthe mixture was washed with water (3×10 mL) and brine (2×10 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe residue was then washed with ether (2 mL)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-cd327757b8ee494fabab218089ea018b
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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